trimethylamine-carboxyborane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: trimethylamine-carboxyborane
• 英文别名: N,N,N-trimethylamine carboxyborane；Me3N*BH2CO2H；borobetaine；boranylformic acid;N,N-dimethylmethanamine
• 化学式: CH₃BO₂*C₃H₉N
• 分子量: 116.956
• InChiKey: WXLFRZRGSPLPEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.52
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trimethylamine-carboxyborane 生成 methylamine-carboxyborane
  参考文献：
  名称：

  SPIELVOGEL, BERNARD F.;MCPHAIL, ANDREW T.;HALL, IRIS H.

  摘要：

  DOI：
• 作为产物：
  描述：

  trimethylamine-cyanoborane adduct 在 triethyloxonium fluoroborate 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以54%的产率得到trimethylamine-carboxyborane
  参考文献：
  名称：

  N-Pyridinyl-indole-3-(alkyl)carboxamides and derivatives as potential systemic and topical inflammation inhibitors

  摘要：

  N-substituted-(indol-3-yl)carboxamides 10-15 and alkanamides 16-18 were prepared starting from the corresponding acids. and submitted to screening for evaluation of their anti-inflammatory activity. None of the considered carboxamides exhibited significant inhibitory effect in the carrageenin-induced rat paw oedema after oral administration of 0.1 mM kg(-1); nevertheless introduction of an alkyl chain, leading to alkanamides 16-18, induced moderate to high activity: 46-95% inhibition. The efficacy of these compounds in the inhibition of topical inflammation was confirmed by measuring reduction of ear thickness in the acute tetradecanoyl phorbol acetate (TPA)-induced mouse ear swelling assay. Preliminary pharmacomodulation brought to the fore that toxic effects induced, at 0.4 mM kg(-1), by N-(pyridin-4-yl)(indol-3-yl)propanamide (17) could be attenuated or suppressed by 5-fluorination or introduction of a methoxycarbonylborane moiety, leading to 18 and 21. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01242-9

文献信息

• Creation of New Boron–Carbon Bonds by Dichlorocarbene Insertion into the Boron–Hydrogen Bond of Amine– and Phosphine–Boranes
  作者：Laurence Monnier、Jean-Guy Delcros、Bertrand Carboni

  DOI：10.1016/s0040-4020(00)00565-2

  日期：2000.8

  A simple approach for constructing a new boron–carbon bond by direct insertion into the B–H bond of amine– and phosphine–borane complexes is described. The outcome of this reaction was studied according to the substituents and the experimental conditions. A preliminary investigation of the reactivity of some insertion products as well as their anti-proliferative activities is also reported.

  描述了一种通过直接插入胺-和膦-硼烷配合物的B-H键来构建新的硼-碳键的简单方法。根据取代基和实验条件研究了该反应的结果。还报道了对某些插入产物的反应性及其抗增殖活性的初步研究。
• Synthesis and examination of amine-cyanocarboxyboranes, the boron analogues of α-cyanocarboxylic acids: X-ray structural study of the first lactam containing a boron atom in the lactam ring
  作者：Béla Győri、István Lázár、Zoltán Berente、Róbert Király、Attila Bényei

  DOI：10.1016/j.jorganchem.2004.06.066

  日期：2004.11

  The first representatives of chiral boron atom-containing amine-cyanomethoxycarbonyl boranes (A . BH(CN)COOMe) have been synthesized either from the corresponding amine-bromocyanomethoxycarbonylborane complexes with [BU4N]CN or from Me3N.BH(CN)COOMe and an amine in a base-exchange reaction. Acid hydrolyses of methyl esters generated the free acids (A.BH(CN)COOH), which are isoelectronic to the alpha-cyano carboxylic acids. Their pK(a) values and hydrolysis half-lives in acidic medium (that is rate of proton reduction) have been determined. Similarly to the alpha cyano carboxylic acids, the cyano group attached to the boron (in alpha position to the COOH group) increased the acid strength of carboxy boranes with 2.0-2.5 orders of magnitude. Independently from the type of the amine, pK(a) values of the amine-cyanocarboxyhoranes (6.34-5.82) decrease consistently with the increase of pK(b) values of the amines. Hydrolytic decomposition rate of the alkylamine complexes increases with increasing pKb values of the amines while the opposite was found for pyridine base complexes. When considering both types of the amines, hydrolysis half-lives of the complexes range over several orders of magnitude from 0.005 to 400 h. Based on these observations protonation of the amine nitrogen atom appears to be the rate determining step in the hydrolysis process. With loss of methanol, 2-NH2-py.BH(CN)COOMe transformed into a five membered lactam derivative. X-ray diffraction revealed that the pyridine ring is coplanar with the five membered lactam ring. In the crystal two molecules are connected in a head to tail arrangement by strong intermolecular H-bonds between N(2)-H and the carbonyl oxygen (01) with a donor and acceptor distance of 2.867(3) A. Three new cyanomethoxycarbonylborates having the composition of K[BHn(CN)(3-n)COOMe] (n = 1, 2) and K[B(OH)(CN)(2-) COOMe] have also been synthesized and their properties examined. (C) 2004 Elsevier B.V. All rights reserved.
• Spielvogel, Bernard F.; Ahmed, Fahim U.; Silvey, Gary L., Inorganic Chemistry, 1984, vol. 23, # 25, p. 4322 - 4324
  作者：Spielvogel, Bernard F.、Ahmed, Fahim U.、Silvey, Gary L.、Wisian-Neilson, Patty、McPhail, Andrew T.

  DOI：——

  日期：——
• Norwood III, Verrill M.; Morse, Karen W., Inorganic Chemistry, 1988, vol. 27, # 2, p. 302 - 305
  作者：Norwood III, Verrill M.、Morse, Karen W.

  DOI：——

  日期：——
• Mittakanti, Mallaiah; Morse, Karen W., Inorganic Chemistry, 1991, vol. 30, # 10, p. 2434 - 2437
  作者：Mittakanti, Mallaiah、Morse, Karen W.

  DOI：——

  日期：——